Wisconsin Vacations & Trips from ₩544,118

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Top destinations in Wisconsin

Milwaukee Art Museum featuring art and modern architecture
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Milwaukee

Milwaukee

The Latest Wisconsin Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

3 out of 5
Downtown Chicago
Price was ₩657,820, price is now ₩544,118 per person
₩544,118
per person
Mar 6 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Montgomery (MGM) to Chicago (ORD)
8.8/10 Excellent! (1,555 reviews)
The staff were friendly and very helpful when checking in or needed help during my stay. The rooms were clean and up to date.

Reviewed on Jan 12, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ₩841,634, price is now ₩578,395 per person
₩578,395
per person
Mar 6 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Montgomery (MGM) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Cleanliness, exceptional customer service, and a complimentary upgrade made our stay outstanding! The way the buffet staff efficiently managed the line, guided guests to tables, and consistently kept the food fresh—all while wearing genuine smiles—was truly impressive. Our room was spotless, modern, and well-stocked, exceeding our expectations. We will definitely be back!

Reviewed on Jan 11, 2026

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was ₩827,394, price is now ₩658,103 per person
₩658,103
per person
Mar 6 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Montgomery (MGM) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Great stay fir early flights

Reviewed on Jan 8, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was ₩738,239, price is now ₩595,602 per person
₩595,602
per person
Mar 6 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Montgomery (MGM) to Chicago (ORD)
8.8/10 Excellent! (3,098 reviews)
I enjoyed that the room had snacks available for purchase at affordable prices. That is very convenient. Room was clean and properly stocked.

Reviewed on Jan 12, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was ₩733,186, price is now ₩593,931 per person
₩593,931
per person
Mar 6 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Montgomery (MGM) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
Clean room, amazinggggg views, everyone was so nice. Must go downstairs to Toro and get a martini from John!!

Reviewed on Jan 10, 2026

Where to stay in Wisconsin

Find the best Wisconsin areas and neighborhoods for the activities you enjoy most. Learn more about Wisconsin
Milwaukee

Downtown Milwaukee

Central business district with cultural, financial, and historical landmarks, Downtown Milwaukee offers shopping at The Shops of Grand Avenue, art galleries in the Historic Third Ward, high-end dining, and vibrant nightlife. Explore the Milwaukee Public Market and Riverwalk, or hop on the free streetcar system.

Find hotels in Downtown Milwaukee

Wisconsin Hotel Deals

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
424 E Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is ₩241,538 per night from Jan 22 to Jan 23
₩241,538
₩284,774 total
Jan 22 - Jan 23
includes taxes & fees
9.4/10 Exceptional! (1,876 reviews)
Mia at front desk was super sweet and helpful. Room was great as well.

Reviewed on Jan 12, 2026

The Pfister Hotel
Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
139 E Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is ₩237,543 per night from Jan 14 to Jan 15
₩237,543
₩280,076 total
Jan 14 - Jan 15
includes taxes & fees
9.6/10 Exceptional! (2,515 reviews)
Great hotel! So fun and unique. Very clean and personalized

Reviewed on Jan 11, 2026

Saint Kate - The Arts Hotel
The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
9.4/10 Exceptional! (3,437 reviews)
Amazing property. Will be back n

Reviewed on Jan 11, 2026

Get rates
The Madison Concourse Hotel and Governor's Club
See all 15,491 properties in Wisconsin
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a Wisconsin vacation package cost?
Starting from as low as ₩544,118, a package is your portal to low-cost travel. Custom make your Wisconsin adventure by choosing from our extensive range of flights, hotels and rental cars.
How do I get a cheap travel package to Wisconsin?
Bundling your flight and hotel with Expedia won't just save precious time — it'll save you cash too. A Wisconsin vacation package makes it easy to organize your dream adventure. With more than 550 airlines throughout the world to choose from, finding convenient flights that fit your busy schedule won't be an issue. Not only that, we've got over 1,000,000 properties globally to select from. Talk about choice! No matter who you are, Expedia puts the world within your reach.
Where should I stay in Wisconsin?
Milwaukee is a fantastic place to include in your itinerary. It's where you'll find impressive sights such as Milwaukee Art Museum and American Family Field. Madison also attracts many jetsetters eager to explore some of the best attractions in Wisconsin. Some of the best are University of Wisconsin-Madison and Camp Randall Stadium.
What are the top hotels in Wisconsin?
Potawatomi Hotel & Casino and Best Western Plus Milwaukee Airport Hotel & Conference Ctr know how to make their guests feel at home in Milwaukee. If your itinerary also includes Wisconsin Dells, take a look at Inn of the Pines and Silver Spruce Resort. Both are popular with travelers.
How far in advance should I book my Wisconsin vacation?
Savvy travelers will likely want to reserve their seats as early as possible. You can normally compare international fares on Expedia up to a year before your intended flight. If you're booking at the last minute, fear not. Low prices occasionally become available just weeks before departure dates.
What does an Expedia Wisconsin travel package include?
Expedia has all you need to arrange your Wisconsin getaway, but what your package looks like is totally up to you. Choose from a combination of hotels, flights and rental cars. Searching for some activities to fill in your time? Once you've made your booking, you can add them on too. No matter your style or budget, there's a package deal to match your needs.
What should I know before booking a Wisconsin travel package?
Discover deals to match your budget with an Expedia package. Flights, hotels, rental cars — we have everything you need to plan your break. You'll save a tidy sum just for bundling your bookings. Whether you're taking off on a ski trip or sunning yourself on a warm beach, your ideal vacation is only a few clicks away.
Can I choose my airline with a Wisconsin Expedia vacation package?
Yes, you sure can. We have more than 550 partner airlines globally, so go with the carrier that suits your needs.
If I'm not able to travel, can I cancel my Wisconsin vacation package?
Certainly, and we'll help you every step of the way. You may be able to cancel and rebook your Wisconsin vacation package for free if you booked in the last 24 hours. But you may incur a fee from your airline, hotel or car rental company if your booking is older than that. If life gets in the way of your vacation, look up our Customer Service Portal for more information.

Discover the most popular places to visit in Wisconsin

Christmas Mountain

Hit the slopes at Christmas Mountain during your trip to Wisconsin Dells. Stroll along the area's riverfront or experience its entertainment choices.

Christmas Mountain

Resch Center

Catch an event at Resch Center during your trip to Ashwaubenon. Stroll along the riverfront or attend a sporting event in this family-friendly area.

Resch Center
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.